


Minefields

by ilithiyarys



Category: Chicago PD (TV)
Genre: Canon Compliant, Canon-Typical Violence, Dark whumpy Hailey, Emotional Hurt/Comfort, F/M, Hurt/Comfort, Season 8 thematic/arc speculation, Season 9 thematic/arc speculation, Upstead, speculative fic
Language: English
Status: In-Progress
Published: 2021-03-15
Updated: 2021-03-19
Packaged: 2021-03-24 05:21:45
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 4,296
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30067296
Author URL: https://archiveofourown.org/users/ilithiyarys/pseuds/ilithiyarys
Summary: After a young woman is kidnapped, Hailey becomes emotionally involved and in an effort to find her, she goes undercover but at what cost?
Relationships: Jay Halstead/Hailey Upton
Comments: 6
Kudos: 64





	1. Chapter 1

The door to Hailey’s apartment slammed open as the two of them frantically moved in unison, passionately kissing, heavily breathing, and giggling while removing their clothes and throwing them all over the apartment. 

They’d just gotten home from celebrating their six month anniversary - a milestone for the both of them given their track record of  _ ‘dating in the workplace.’ _ Neither of them had managed to hold down a steady relationship.

Until now, that is.

The two of them were enjoying their time at a fancy restaurant in downtown Chicago,  _ The Capital Grille _ , which had quickly become one of their favourites ever since restaurants and sit-in dining became available again. It had a gorgeous view of Lake Michigan on one side, and the Chicago skyline along the other. They’d both gotten tipsy from the amount of wine and whiskey they’d had celebrating their little milestone. The whole day was perfect, despite them having to go to work. Jay had planned the whole thing, reminiscing how they’d started their day.

_ The warm sunlight fell on Hailey’s face, and the aroma of fresh coffee filled the room. A gentle hand reached for her face, waking her up. _

_ “Happy anniversary,” he grinned. _

_ Hailey giggled. “Babe, we’ve only been together six months. We’re at the halfway mark to our one year anniversary,” _

_ Jay shrugged, handing her a coffee mug. “Yeah, but this is the longest and healthiest consecutive relationship I’ve been in, so it’s kind of a big deal to me,” _

_ The blonde smiled, leaning in to kiss him. _

_ “You’re a big deal to me,” she whispered, gently biting at his lip. _

_ She put the coffee mug back on the side table, as the brunette initiated another kiss, crawling back into bed with her. _

_ They hadn’t gotten very far before their phones began to vibrate. Hailey groaned, laughing at the bittersweet timing. _

_ “I swear, this happens every time!” she exclaimed, holding both sides of his face, kissing him gently before breaking away for them to check their phones. _

_ “Don’t worry, I’ve got a surprise planned for us tonight. We’ve just gotta get through today,” _

_ “I’ll hold you to that,” she grinned. _

_ “Happy anniversary, hon.” _

_ “Happy anniversary, babe,” _

Jay thought he’d covered his bases throughout the day by leaving small gifts in her desk, in her locker, and even a dress he’d picked out for her before surprising her with an evening out - something they’d rarely done throughout the entirety of their relationship. But it wasn’t until Hailey let slip the fact she too, had a surprise waiting for him at home after dinner was over.

From then, it was a race (a safe,  _ uber _ race) to get back to her place, because honestly, Jay could  _ not _ wait.

He led the two of them onto the couch, both of them already half-undressed before Hailey leaned in to kiss him one more time.

“Wait here, I’m gonna slip into something more comfortable,” she winked. Jay bit down on his lip, eagerly anticipating what possibly his beautiful girlfriend would come out wearing. What felt like an eternity later (though in reality, was only three minutes), Hailey whispered for him to come back to the bedroom.

Jay opened the door to find her laid out on the bed dressed in incredibly sexy lingerie.

“Sweet Jesus,” Jay nearly squeaked under his breath, already crawling on the bed. His lips found the sweet spot on her neck that elicited a subtle moan from her. It was intoxicating. She began undoing his belt to remove his pants, reciprocating his hungry kisses. 

No more than two minutes later, both their phones began going off.

“No, no!” Jay complained mid-kiss, groaning. “Why the hell does this keep happening to us? I swear to God, we need to throw our phones in a safe whenever we engage in any kind of sexual activity,” 

Hailey let out a hearty laugh, kissing him once more before reaching for her phone. “You don’t have to tell me twice. At least we’re doing other things outside of work now,”

“Yeah, that being each other,” he smirked. Hailey giggled, gently punching him in the arm. “I just hate that whatever  _ this _ is just interrupted our sexy time,” he pouted, pointing his finger at his phone.

The blonde grinned. “Come on, you know there’s going to be plenty more of  _ this _ ,” she said, looking down at her outfit.

Jay bit his lips.

“So what do we have?” he sighed, chucking his phone aside. Hailey had hers out anyway, they would have gotten the exact same notification. 

The blonde’s spine straightened from her slumped over posture to grab her phone off the side table. “Damn. It’s a kidnapping. We gotta go babe,” Hailey said, already making her way off the bed and into the bathroom. Jay quickly followed, grabbing a different pair of pants from his drawer in her closet. He hadn’t quite officially moved in with Hailey yet, but they might as well have been living together at this point. He had a trunk full of his stuff already at her place, and they’ve spent nearly all their time at her apartment. He’d offered his own to share the nights to stay at early on when they started dating, but Hailey had seen his tiny apartment-slash-man cave, and even he felt more comfortable at her place anyway.

He’d finally gotten an acceptable work ensemble on, meeting Hailey just as she exited the bathroom wearing her usual fit as well: blue jeans and a flannel.

“Are you good to drive?” she asked.

“Yeah, let’s go,” he nodded, attaching his badge and gun onto the waistband of his pants. 

No more than twenty minutes later they arrived at the district, running up to the Intelligence bullpen. It was frustrating that they’d picked up this case at 10:30pm, but a kidnapping was time-sensitive. Voight took the case as soon as it came in.

The two of them greeted the rest of their colleagues and Sergeant, who all had been waiting on them. It wasn’t a surprise that everyone knew that they were dating at this point. Voight had found out almost immediately when he’d heard Hailey and Jay bickering one day about some speech that Jay had made talking to their suspect, and Hailey going off about how he didn’t know the half of what she’d gone through. As soon as they’d wrapped the case, Voight invited them into his office, laying out HR forms on his desk for them to fill. They were surprised their Sergeant found out the literal day after they’d slept together and anticipated them being together long enough for him to already be giving them forms to fill out. What was more surprising though, was the fact he wasn’t splitting them up or transferring one of them out. He said something along the lines of, “just as long as you two can keep it together at work that won’t jeopardize each other or the rest of the team. Leave the home stuff at home.” To that, they agreed, strictly staying professional on the job.

However, it wasn’t long after until their coworkers started to suspect that something more was going on between them: worried looks while one was undercover, the subtle reaches and touches, the eye contact and gentle smiles. It was different from their normal “partner affection.” No, it was deeper. Kevin was the first to find out, then Kim, then Adam. Even their newest addition to the unit, Cooper, could sense that there was something between the Detectives. Soon everyone knew and accepted it. Hell, nearly everyone’s reactions were the same saying in their own little way,  _ “it’s about damn time.” _

From then, Jay and Hailey felt a lot more comfortable knowing that they didn’t have to tiptoe around each other anymore at work, or be worried about a possible slip up revealing that they were together. They were free to just be themselves.

“What’s the situation?” Hailey asked.

Kim was the first to update them. “Mia Collier, twenty-five years old, student at the University of Chicago. She was kidnapped right in front of the department store she worked at after finishing her shift just thirty minutes ago,”

“Security footage from the parking lot caught the whole thing. Unable to get a plate from the vehicle, they knew exactly where the cameras were,” Adam added.

Kevin waved everyone over to his desk, pointing at his computer screen. “Traffic cams caught them heading westbound, but footage eventually ran out. They’re in the wind,”

They all looked to their Sergeant for their next move. “Okay. Jay, Hailey, head to Mia’s apartment complex and speak to the building manager to check out her apartment. See what you can find. The rest of us will keep digging for leads. Listen, we’ve got a missing young woman, and we don’t know what the motive is for kidnapping her yet. But assume we’ve got a twenty-four hour window before things get worse. We move quickly to bring this girl home alive,”

A chorus of  _ yes, Serge’s _ rang through the bullpen before everyone went on to do what they were ordered to.

About fifteen minutes later, Jay and Hailey arrived at Mia’s apartment complex. The building manager had been kind enough to give them a set of keys to her apartment. It was on the sixth floor of the building, so the detectives moved quickly up the elevator and through the halls.

When they’d reached Mia’s unit, the door was slightly open. 

Someone had already broken in.

They drew their guns, silently communicating their plan of execution. Jay counted to three with his fingers, pushing the door open for Hailey to move in first.

Like a well-choreographed dance, they swiftly moved through the apartment to clear the rooms. 

“Looks like we just missed whoever was here,” Hailey announced.

The apartment was completely flipped upside down: furniture pushed to the ground, papers, books, magazines were scattered all over the floor. Mia’s bedroom was a complete mess.

“What the hell were they looking for?” Jay wondered.

“Jay, over here. Blood,” Hailey clenched her jaw, pointing to a small smear of blood on the doorframe of Mia’s room.

“That could be a lead,” the brunette observed.

Hailey nodded. “Yeah, I just called for the crime lab. Just hope it isn’t hers,”

“Yeah,” Jay agreed.

Although they hadn’t said it out loud, the question hung in the air between the two of them.

_ What had this girl gotten herself into? _

Back at the district, Kim, Adam, and Kevin worked quickly to dig into Mia’s life. Jay and Hailey had security footage from the building sent over to the team back at the district, confirming that Mia was taken from work, back to her apartment, held at gunpoint. 

Once again, they knew where the cameras would be, avoiding their plates and their faces to be caught on camera. The detectives updated the rest of the team that because these guys knew exactly where the cameras were at both Mia’s work and home, that they must have been surveilling her for a while. They had weeks worth of footage sent back to them to work through.

There were three masked assailants - one driving the getaway van, and the other two handling the young woman. One had kept watch to make sure they could enter the building without being caught by the building manager; that’s how they’d managed to break into her apartment. As they fast-forwarded through the footage, they saw that the assailant had a bloody nose - Mia managed to strike him in the nose, giving them a lead with the blood Hailey had found on the doorframe. Unfortunately, the rest of the footage didn’t give them much to work with. Mia and the assailant left her apartment empty-handed, which means she was hiding something from them if they hadn’t killed her yet.

There was hope. She was still alive.

But the bad news was that she was now probably being tortured for information, tortured to find whatever these guys were looking for.

**Notes for the Chapter:**

> well, this was originally supposed to be a speculative one-shot for what i think is gonna happen at the end of s8 but then it ended up becoming its own thing and i'm actually pretty stoked about it. thanks for reading!


	2. Chapter 2

**Notes for the Chapter:**

> here's chapter 2! trying to get this story updated as often as i can - i'm still using this story as part of my own speculation of the themes and parallels of what i think might happen towards season 8 going into season 9; but instead of speculating the actual details, pay attention to what i'm doing with jay and hailey in their relationship and dynamic.

Hailey and Jay returned to the district a few hours later after talking to various witnesses in Mia’s apartment building. Everyone said the same thing about her: she was sweet, quiet, hard working, and didn’t seem like the type to be caught up in anything shady to be kidnapped over.

It was just past midnight at this point, and everyone had begun to feel the fatigue and exhaustion settle in. They’d basically worked a double shift, finishing at around 5pm the previous day, only to be called back in five hours later. Jay and Hailey knew that the rest of their team would be on edge from working an all-nighter case, so on their way back they’d bought two cases of coffee and a dozen donuts from Dunkin’ Donuts, one of the only places they could find that was serving coffee this late at night.

Everyone’s faces lit up at the sight of them two walking in with the goods.

“Yes!” Adam cheered, rushed out of his seat to grab one of the coffee jugs from them.

“Our heroes,” Kim added, taking a break from staring at her computer. Kevin and Andre quickly followed, also eager for a cup of coffee. Jay and Hailey laughed, placing the coffee and donuts on one of the unused desks.

“So where are we at? Find anything new?” Jay asked.

Kim nodded, pouring herself a cup of coffee. “Dug into Mia’s family history. Tragic story. She lost her parents and grandparents when she was young. They were in an accident in their family vehicle, and she and her brother were the only survivors.”

“The two of them had godparents that they’d stayed with until Mia was of legal age to take care of her younger brother, Aiden, and the two of them moved out soon after,” Cooper added.

Adam continued. “Then her brother fell ill a few years later. He was diagnosed with leukemia. It looks like she tried to take care of the bills for his treatment.”

Jay began to piece it together. “So it’s safe to say that she was probably struck for cash to pay off her college tuition and her brother’s medical expenses?”

“It seems so,” the officer nodded.

“What happened to her brother?” Hailey asked. 

Adam frowned. “He passed recently. Just over a month ago. The worst part is she wasn’t allowed to see him or be with him when he passed because of COVID.”

Everyone had collectively let out a sigh of sadness, shaking their heads and clenching their jaws. They felt bad for the young woman. She’d already been through hell losing her entire family, only to lose the one person had left and couldn’t even be with him until his last breath. Hailey felt a looming sadness come over her, something stirring in the pit of her stomach. She barely even knew this young woman, but already felt so deeply for her. Although their situations were different, she knew all too well the feeling of living through hell and trying to take care of a younger sibling on your own.

“Could that explain her financial situation?” Jay asked.

Kevin nodded. “Yeah. She was behind on this month’s rent payment, working two jobs to make ends meet. Her building manager mentioned that she was normally pretty good with making payments on time, it just so happened that she was a few days late this month. Also found large amounts of money being randomly deposited and then immediately taken out via cash withdrawal. A red flag.”

“Any leads on the blood from the doorframe in Mia’s room?” Hailey asked.

Andre nodded. “Yeah, just got the lab results back. Blood belongs to Travis Williams. Linked to a few B&E’s, robberies but nothing conclusive. He’s suspected of being a part of this new crime ring, but again, nothing conclusive.”

“What’s special about this new crime ring?” Kim questioned.

Hank responded, coming out of his office having heard the team’s updates. “They’re smart. They’ve brought drug trafficking and dealing, weapons trafficking and dealing, and money laundering together to fund their activities.”

“So how come they haven’t been taken down yet?” Jay asked.

Hailey answered this time. She knew of this new crime ring from a tip she’d gotten from one of her CI’s. “No one knows where they operate or who their leaders are or even what they’re called. It’s a tight knit operation. Last I heard was that they don’t operate in just one area, but multiple. Fanning out means less attention.”

“I’ll talk to guns and gangs to see what else they’ve got on these guys,” Hank noted.

“Serge, mind if I come with?” Hailey asked. Everyone stopped to turn around and look at the blonde detective. It was strange that she was willing to hop with Voight for something. Even Jay glanced over, furrowing his brow at his girlfriend.

But instead of questioning her, Voight just grunted. “Okay.”

Hailey nodded.

Hank continued on. “Halstead, bring Ruzek with you to find this Travis character and bring him in. The sooner we find this girl, the better.”

The rest of the team nodded, returning to work.

“Hailey, with me,” the unit sergeant said, leading them to the parking lot.

* * *

The moment the pair had gotten into the SUV, Hank looked over at his detective. “What’s going on, Hailey?”

“Nothing, just wanted to ride along,” She answered.

“Halstead do something?” He asked. He wasn’t quite sure what was going through his detective’s mind right now.

Hailey knitted her brows, shaking her head. “What? No, we’re good. Just wanted to tag along with you.”

“Hailey, there’s something you’re not telling me,” he said in a low voice.

She sighed. “I think I’ve got an angle to play.”

“Please elaborate,”

“If Mia had gotten caught up with this crime ring, it probably means they’re looking for women to help front their operation. Large sums of cash being deposited and withdrawn? It seems like she’s laundering money for them, and in return, they’re paying her, probably off book to help pay for whatever debts she has,” she speculated.

“So what are you suggesting?” Hank questioned.

“Let me go under. Women are the most unassuming for these kinds of jobs, which is why I’m thinking why they’ve been so successful. Mia is the exact kind of person they’re looking for to help run their operation - a young woman with a steady job, a relatively normal life, no family, nowhere to go, and nowhere to run. She would’ve easily gotten involved needing extra cash to pay her debts. I have a CI that’s acquainted with these guys, I could probably get an intro to one of their higher ups, get an in, try to find Mia and get her out,” the blonde explained.

The unit sergeant gave her a warning look. “Hailey… What you’re suggesting is incredibly dangerous. We don’t have much intel on these guys and how they run things,” Hank cautioned.

Hailey nodded. “Serge, I know. That’s why I wanted to come with you to find out what else guns and gangs know.”

The older man grunted. “Okay. But I need to know, is your head on straight? Or are you saying this because you empathized with Mia’s situation because of how similar her life is to yours?”

For a moment, Hailey’s stomach dropped. Her boss could read her like an open book. She knew he'd seen her file growing up: abusive father, getting out of the house as soon as she turned eighteen, taking legal custody of her brother because they’d been able to prove they were abused and raising him all on her own. Hailey knew what it was like, what Mia would’ve gone through.

But instead of getting defensive, she calmly responded.

“Serge, a young woman is missing and involved with the wrong crowd. I just want to help find and bring her home. I’m good, I promise.”

“Okay.”

Across the city, Jay and Adam had tracked Travis’ last known location to a house out in West Englewood. It didn’t slip past them that this was one of the most dangerous neighbourhoods in the city, so they’d geared up in their vests as a precaution.

Jay knocked on the door. “Travis Williams! Chicag-”

Before he could even continue his sentence, gunshots rang out and bullets flew through the door and windows, forcing the pair to the ground.

“10-1, shots fired at the police!” Adam shouted into his radio. “You good?” Jay asked, helping the officer up, as he spotted someone running out back. “Yeah, I’m good,” Adam nodded.

“5021 George, in pursuit of an offender, send patrol to 352 South Ashland Avenue, our offender is Travis Williams, 5’10, short brown hair, medium build, black hoodie and blue jeans,”

_“Copy, sending patrol now.”_

Jay and Adam sprinted through the alleys after Travis.

“I’m going around back to cut him off!” Adam shouted, breaking away from the detective. Jay kept up his chase, keeping Travis in his line of sight. Suddenly, he took a sharp turn into an alleyway, escaping Jay’s sight for a moment.

Jay followed, drawing his gun. He couldn’t hear heavy breathing, which was alarming. Travis had either slipped away, or he was waiting for the right moment. He continued down the alley, training his gun firmly ahead of him.

Then out of nowhere, shots were fired at his direction again, and he felt his breath hitch in his throat as something threw him to the ground. He felt a stinging sensation radiate through his body. 

“Ah!” he hissed, crawling towards cover. He’d been shot. He frantically searched if it had gone through.

Thankfully it didn’t.

Not too long after, he heard Adam over the two-way. _“5021 Ida, suspect in custody.”_

On their department-issued phones, Adam called for Jay. _“Jay, you good? I heard shots, where are you?”_

He slowly reached for his phone that was in his vest pocket. “Just down the same alley. Caught one in the vest.”

 _“Copy, I’m on my way,”_ Adam responded. On his two way, he’d called out for an ambulance. _“5021 Ida, officer injured. Roll an ambo to my location ASAP.”_

A minute later, the younger officer appeared. He offered out his hand to the detective, slowly helping him up off the ground. Jay yelped, already feeling the bruising starting to settle in on his abdomen.

“Hailey’s not gonna be happy you got shot again,” Adam quipped.

“Yeah, yeah, I know. I’m trying not to think about it,” Jay grimaced, slightly hunching over to relieve his body of the pain. He knew how strongly Hailey felt when he would get injured on the job. They’d always feared it even before they started dating, but ever since, they both had a heightened sense of fear for one another whenever one of them was injured. He just happened to be more of a bullet magnet than his girlfriend was. Though his vest had protected him, he could already see her worried face. He tried not to think about it. In fact, he was already thinking about what he was going to say to her.

Adam noticed the detective spiraling in his thoughts. “Sorry bro. Good thing we decided to wear our vests tonight. Could’ve gone a completely different direction.”

Jay frowned, realizing how badly tonight could’ve gone had he not been wearing his vest. The wound would’ve been critical if not for the Kevlar that was protecting his body. “Yeah, you got that right,” he shuddered.

The officer motioned for Jay to follow him towards the ambulance that was already incoming. “Come on, let’s head to the ambo.”

He nodded, as Adam gently patted him on the back.

* * *

It was nearly 2am by the time Jay and Adam returned to the district. Kim, Kevin, and Andre heard the whole thing go down on their radios.

“God, are you guys alright?” Kim worriedly asked, seeing the two of them walk up the stairs. Jay was holding an ice pack to his abdomen, slightly hunched over.

“Yeah, yeah. We’re good. Jay took one to the vest, but he’ll be fine. Just a few bruised ribs,” Adam answered.

“Thank God you two were wearing your vests in the first place,” she said.

“Yeah, we’re counting our lucky stars,” Jay breathed.

“Where’s our guy?” Adam asked.

Kevin responded. “Down in holding. Just waiting for Serge to get back before questioning him.”

Shortly after, Hailey and Hank made their way up the stairs. She immediately spotted her boyfriend nursing an ice pack to his ribs.

“Oh my God, Jay, what happened?” she asked, quickly making her way towards him.

He shrugged, trying not to worry her. “I’m fine, just took one to the vest while trying to bring our guy in.”

“How bad?” she asked. He could tell she was desperately battling the tears from falling in front of everyone. He knew how much she hated it when he got hurt, _especially_ if she wasn’t by his side.

“Just a few bruised ribs. Nothing I haven’t experienced before,” he half-smiled, trying to calm her nerves.

Hailey let out a sigh. “Thank God you were wearing your vest.”

The brunette nodded. “Oh believe me, I know. Tonight could’ve gone terribly wrong. We knew we were dealing with someone linked to a dangerous crime ring, it didn’t hurt to proceed with extra caution.”

“I’m glad you’re okay,” she said, looking down and letting out a shaky breath. Jay noticed, gently reaching for her hand, locking his fingers between hers.

“Yeah, me too."

“Glad you’re okay, Jay,” Hank expressed. “Listen, it’s been a long night. Everyone, go home, we’ll pick this up first thing in the morning. Go get some sleep, we’ll reconvene at 8am.”

Everyone nodded. They didn’t need to be told twice.

**Notes for the Chapter:**

> thanks for reading!


End file.
